The People Behind XRT - Billy Webber "The Accidental CEO"

From helper to helm
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Billy, our CEO, recently joined the Blue Sky podcast “Two Pints of Lager and a Spreadsheet” to share his journey as what he calls the “accidental CEO.” In the episode, he talks openly about stepping into leadership during COVID, scaling the company to 16 staff and multiple NHS contracts, and the lessons he’s learned about resilience, culture, and growth along the way. Billy also reflects on future-proofing through people-first leadership, building a strong pipeline, and using AI to empower teams rather than replace them.

Before taking the top job, Billy’s role was to support spinouts—writing plans, finding finance, recruiting leaders. Then the mirror turned. Becoming CEO in the middle of COVID meant embracing ambiguity, not avoiding it. The outcome: a product that evolved far beyond the original spinout brief, real traction across the NHS and private sector, and a growing, distributed team.

You can watch the full episode here.

Snapshot

• 4.5 years in
• 16 staff (he kept saying 15—“I miscounted!”)
• 6 NHS trusts + 6 commercial contracts
• Scaling across the UK → private sector → overseas next

What actually worked (and what didn’t)

1) Pipeline beats prayer

Early on, Billy’s team pinned too much hope on a few “please-let-this-land” deals. Now the rule is simple: line up more than you need. Keep multiple opportunities 80% done so a single “no” never stalls growth.

“Have a lot of emphasis on getting that one thing over the line—and when it doesn’t happen, you’re hit. So get more lined up early.”

2) Plan just enough—then move

Billy’s instinct is to get out, meet people, and execute. As the company matured, planning caught up—but it’s practical, not performative. They now plan for the growth they know, not the product they might be. Strategy follows product-market reality, not the other way round.

3) Culture isn’t a poster, it’s a practice

With people spread nationally, Billy brings teams together regularly to deepen trust and collaboration. The office is dog-friendly (his own pup’s still learning not to leap onto tables). And yes, the best ideas often happen on walks—clarity by fresh air.

4) Grow leaders on purpose

They’re launching an internal Future Leaders Programme so ambitious teammates can apply, learn the craft of management, and avoid the classic mistake of promoting by tenure without tools.

“It’s not fair to promote someone and let them sink. Give them the skills to get the best out of people.”

On resilience (without the burnout badge)

Billy’s done the 12–15 hour days. The lesson isn’t “work less” or “work more”—it’s work intentionally. If long hours are a choice and energise you, fine. If they’re a trap, fix the upstream system: staffing, process, scope.

He also keeps a simple health check: if output drops while hours rise, it’s time to reset. Walks help. So do honest 1:1s. So does saying “not now” to low-leverage work.

AI: amplify the humans, don’t erase them

Billy’s take is pragmatic: AI is a force multiplier, especially for clinicians and knowledge workers. His team uses it to remove drudge, sharpen proposals, and accelerate delivery—not to rip out the human core of the service.

• Use AI to speed the boring and surface the signal.
• Keep clinicians/professionals front-and-centre where judgment and empathy live.
• Share internal AI wins widely—when devs build something not yet client-ready, they demo it internally to lift everyone’s game.

Billy’s advice to founders (and to his past self)

1. Over-create options. Never rely on a single deal. Build a rolling, qualified pipeline so misses don’t matter.
2. Be flexible on the “how,” firm on the “who for.” Let customer reality refine your offer; don’t lock yourself in too early.
3. Invest in managers before you need them. Career paths, coaching, and real tools—so people rise without drowning.
4. Guard the culture of agility. Cross lanes when it serves the customer; discourage “that’s not my job.”
5. Use AI now. Even simple automations deliver compounding advantages. The gap widens fast.

Where Billy’s steering next

• Scale depth in the NHS while expanding private-sector impact.
• International pilots once the UK playbook is repeatable.
• People systems (Future Leaders, cadenced offsites, shared AI toolkits) to grow without calcifying.

Accidental or not, this is what intentional leadership looks like: more options than obstacles, more coaching than control, more walking than hand-wringing—and a pipeline that doesn’t depend on hope.

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